Substituted 3-phenyl-5-alkoxy-1,3,4-oxadiazol-2-ones, their preparation and their use as pharmaceuticals
申请人:——
公开号:US20010031772A1
公开(公告)日:2001-10-18
Substituted 3-phenyl-5-alkoxy-1,3,4-oxadiazol-2-ones of the formula 1 are described,
1
in which R
1
is substituted C
1
-C
6
-alkyl and C
3
-C
9
-cycloalkyl, R
2
, R
3
, R
4
and R
5
are hydrogen, halogen, nitro, C
1
-C
4
-alkyl, C
1
-C
9
-alkyloxy, substituted C
6
-C
10
-aryl-C
1
-C
4
-alkyloxy, C
6
-C
10
-aryloxy, C
6
-C
10
-aryl, C
3
-C
8
-cycloalkyl or O—C
3
—C
8
-cycloalkyl, or 2-oxopyrrolidin-1-yl, 2,5-dimethylpyrrol-1-yl or NR
6
-A-R
7
, with the proviso that R
2
, R
3
, R
4
and R
5
are not simultaneously hydrogen, and at least one of the radicals R
2
, R
3
, R
4
or R
5
is the radical 2-oxopyrrolidin-1-yl, 2,5-dimethylpyrrol-1-yl or NR
6
-A-R
7
, wherein R
6
=hydrogen, C
1
-C
4
-alkyl or substituted C
6
-C
10
-aryl-C
1
-C
4
-alkyl, A=a single bond, CO
n
, SO
n
or CONH, n=1 or 2, R
7
=hydrogen, substituted C
1
-C
18
-alkyl, C
2
-C
18
-alkenyl, C
6
-C
10
-aryl-C
1
-C
4
-alkyl, C
5
-C
8
-cycloalkyl-C
1
-C
4
-alkyl, C
5
-C
8
-cycloalkyl, C
6
-C
10
-aryl-C
2
-C
6
-alkenyl, C
6
-C
10
-aryl, biphenylyl, biphenylyl-C
1
-C
4
-alkyl, indanyl, or the group Het-(CH
2
)
r
—, wherein r=0, 1, 2 or 3 and Het=a saturated or unsaturated 5-7-membered heterocycle, which may be optionally benzo-fused and optionally substituted, and proceses for their preparation. The compounds of formula 1 show an inhibitory effect on hormone-sensitive lipase, HSL.
描述了式1的3-苯基-5-烷氧基-1,3,4-噁二唑-2-酮的替代物,其中R1是取代的C1-C6烷基和C3-C9环烷基,R2、R3、R4和R5是氢、卤素、硝基、C1-C4烷基、C1-C9烷氧基、取代的C6-C10芳基-C1-C4烷氧基、C6-C10芳氧基、C6-C10芳基、C3-C8环烷基或O-C3-C8环烷基,或2-氧代吡咯烷-1-基、2,5-二甲基吡咯-1-基或NR6-A-R7,其中R6=氢、C1-C4烷基或取代的C6-C10芳基-C1-C4烷基,A=单键、COn、SOn或CONH,n=1或2,R7=氢、取代的C1-C18烷基、C2-C18烯基、C6-C10芳基-C1-C4烷基、C5-C8环烷基-C1-C4烷基、C5-C8环烷基、C6-C10芳基-C2-C6烯基、C6-C10芳基、联苯基、联苯基-C1-C4烷基、茚基,或基团Het-(CH2)r-,其中r=0、1、2或3,Het=饱和或不饱和的5-7元杂环,可以选择地与苯融合和可以选择地取代,以及它们的制备方法。式1的化合物表现出对激素敏感的脂肪酶HSL的抑制作用。